3,4-dihydro-2H-pyran → 3-(((2-Tetrahydropyranyl)oxy)methyl)benzaldehyde

HRID 2226981Notes

Reaction equation

HRID 2226981 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7].[CH2:11]1[CH2:16][O:15][CH:14]=[CH:13][CH2:12]1>C(Cl)Cl.CC1C=CC(S(O)(=O)=O)=CC=1>[O:15]1[CH2:16][CH2:11][CH2:12][CH2:13][CH:14]1[O:7][CH2:6][C:5]1[CH:4]=[C:3]([CH:10]=[CH:9][CH:8]=1)[CH:2]=[O:1]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 131314553-(Hydroxymethyl)benzaldehyde

Product 1

HCID 190029373-(((2-Tetrahydropyranyl)oxy)methyl)benzaldehydeYield 87.7%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

This alcohol (0.44 mole) was dissolved in CH2Cl2 (500 ml). DHP (50 g, 0.59 mole) and PTSA (1 g, 5 mmol) were added and the mixture was stirred overnight at r.t. After concentration in vacuo, the residue was purified by flash chromatography (5% to 15% EtOAc in toluene) to give 85 g of the title compound.

Workup

  1. concentrationAfter concentration in vacuo
  2. customthe residue was purified by flash chromatography (5% to 15% EtOAc in toluene)

Sources & evidence

ORD record
ord-40b19419a9f54b579e8050a5ebf51c69
Source dataset
uspto-grants-1994_09
Patent number
US05350760

Reaction notes

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